Paul McCartney shares how he was "always frightened of classical music" and what it was like to be a part of the pop world at the time. James Paul McCartney is an English musician, singer, and songwriter. He gained his fame with the Beatles in the 1960s, and then pursued a solo career from 1970 onward.

Singer Janet Jackson speaks with Oprah for the first and only time about the wardrobe malfunction that exposed her breast at Super Bowl XXXVIII on February 1, 2004. She explains how the accident happened and shares her response to the national backlash she faced for the accident, despite having the nipple covered by a pasty. Jackson says she regrets apologizing for the incident and talks about how it effected what she was working on at the time.

Jack Lemmon, an Academy Award winning actor and musician, discusses Marilyn Monroe and her insecurities during her rise to fame. Lemmon starred in Some Like It Hot with Marilyn Monroe in 1959 and saw her experiences and insecurities in Hollywood in the 1950's and early 1960's first hand.

In a 1997 interview, Paul McCartney discusses how he heard about John Lennon's death. Lennon was assassinated on December 8, 1980 by Mark David Chapman, a man he had earlier signed a copy of Double Fantasy for.

Richie Havens was interviewed in 2009 about his Woodstock experience by Voice of America's Adams Phillips on the 40th anniversary of the festival. Havens discuses Woodstock's unique atmosphere and his memories of the festival.

Musician Carlos Santana remembers how he got the chance to play at Woodstock and recalls the most memorable moments of his performance.